N-bromobutanimide → HCID 73863377, compound

HRID 1828372Notes

Reaction equation

HRID 1828372 reaction equation
[CH3:1][O:2][N:3]=[CH:4][CH2:5][NH:6][C:7]([C:9]1[CH:31]=[CH:30][CH:29]=[CH:28][C:10]=1[C:11]([NH:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]([F:26])([F:25])[C:21]([F:24])([F:23])[F:22])=[CH:16][C:15]=1[CH3:27])=[O:12])=[O:8].BrN1C(=O)CCC1=O.[I:40]N1C(=O)CCC1=O>>[I:40][C:31]1[C:9]([C:7]([NH:6][CH2:5][CH:4]=[N:3][O:2][CH3:1])=[O:8])=[C:10]([CH:28]=[CH:29][CH:30]=1)[C:11]([NH:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]([F:25])([F:26])[C:21]([F:24])([F:23])[F:22])=[CH:16][C:15]=1[CH3:27])=[O:12]

Participants

4

Reactant 3

HCID 67184N-bromobutanimideHCID 120273N-IodosuccinimideHCID 73863378HCID 73863378, compound

Product 1

HCID 73863377HCID 73863377, compoundYield 53%

Procedure

2-(2-(N-methoxyimino)ethylaminocarbonyl)-2′-methyl-4′-pentafluoroethylbenzanilide was treated in the same manner as in Example 36, except that the N-bromosuccinimide was replaced with N-iodosuccinimide, to obtain 3-iodo-2-(2-(N-methoxyimino)ethylaminocarbonyl)-2′-methyl-4′-pentafluoroethylbenzanilide (yield 53%, melting point 110° C.). Regioselectivity of iodination into the 3-position was 100%.

Sources & evidence

ORD record
ord-f503fad969ed4b28afdfed295828c4a3
Source dataset
uspto-grants-2006_06
Patent number
US07057067B2

Reaction notes

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